Hydrochloric Acid → 1-(3-tert-Butyl-5-iodo-4-methoxyphenyl)ethanone
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:13](=[O:15])[CH3:14])[CH:8]=[C:9]([I:12])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].CI.[C:18](=O)([O-])[O-].[K+].[K+].Cl>O.C(OCC)(=O)C.CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([C:13](=[O:15])[CH3:14])[CH:8]=[C:9]([I:12])[C:10]=1[O:11][CH3:18])([CH3:4])([CH3:2])[CH3:3]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
1-(3-tert-Butyl-4-hydroxy-5-iodophenyl)ethanone (616 mg, 1.93 mmol) was added to N,N-dimethylformamide (2.5 mL), and then methyl iodide (684 mg, 4.84 mmol) and potassium carbonate (401 mg, 2.90 mmol) were added, followed by 3 hours of stirring at 60° C. After cooling the mixture to room temperature, ethyl acetate (6 mL), water (3 mL), and 2 N hydrochloric acid (2 mL) were added, and the solution was separated. The organic layer was washed with a mixed solution of water (3 mL) and saturated brine (1 mL), followed by saturated brine (3 mL). The organic layer was dried and concentrated under reduced pressure (50° C.) to obtain 587 mg of the subject compound as a yellow oily substance (yield: 91.3%, HPLC purity: 94.1%).
Workup
- temperatureAfter cooling the mixture to room temperature
- customthe solution was separated
- washThe organic layer was washed with a mixed solution of water (3 mL) and saturated brine (1 mL)
- customThe organic layer was dried
- concentrationconcentrated under reduced pressure (50° C.)
Sources & evidence
- ORD record
- ord-11ba448b7d8945fb8f77ffa594d4acbc
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375236B2
Reaction notes
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